Night of Tricks
by SlashAddx
Summary: Damon reluctantly agrees to an elaborate game of role playing as a prostitute to shake up his romantic life with Stefan. He doesn't have any idea what's in store for him. / Established Defan, eventual vampcest, more warnings in first chapter, basically just smut. ;)
1. The pick up

_Warnings include: language, prostitution, blood-sharing, not-quite-explicit sex, and constant mentioning of established Damon/Stefan relationship._

Inspiration: Damon in a leather vest.

* * *

 _What the hell?_

Damon ran his hand over his bare stomach and adjusted his vest. His fucking leather vest. The dank odor of the wet roads and the smells he didn't want to think about coming from the ally were upsetting. This was an insipid idea. He was Damon fucking Salvatore. And here he was in tight black leather pants and an open vest whoring himself out like a cheap trick. This was the worst idea Stefan ever had. It was supposed to be some sort of experiment. Stefan was convinced Damon was getting bored with their sex life. Hardly true, but Stefan wouldn't believe him, so naturally he gave in to his brother's whims. Now here he was dressed like an escaped slave from some S&M club, loitering on the street, and supposedly picking up a new partner for the night. No trace of Stefan since his brother dropped him off and drove away in the Camero a half hour ago.

It's not like they had been remotely monogamous in their lifetimes, but this one-sided role-playing lost a little something in the translation. If this were a real profession he would have done it right. Full tailored suit, maybe a cane. Better shoes. Perched in a hotel bar, not walking the streets in the middle of the night.

 _Fuck._

He stopped pacing as a black sedan turned the corner towards him. There weren't many reasons people drove to this street in this part of town. They were all looking for some company but it only took half a glance for Damon to be disinterested. The car was all wrong. Generic people drove generic cars and the only reason Damon agreed to this was because Stefan convinced him he'd probably get dirt on someone interesting. He was already rolling his eyes.

The car slowed to a stop in front of him and the tinted passenger window slid down a crack. A balding middle-aged man leaned over, squinting, as he looked Damon over. Fucking pig. He looked like a suburban dad, nervous and horny. "How much?"

Damon scoffed. "If you have to ask you can't afford it."

The creep's face flushed bright red, even in the dark. "Do you take cards?"

Shit, a first timer. Bending down to look into the car with his arms crossed tight over his chest Damon practically growled. "Fuck no, I don't take plastic. What do you think this is? Besides what would you tell the wifey when 'Back Ally Fuck' showed up on your Visa statement?" The rhythm of the guy's heart picked up and tempted Damon for something entirely different. This wasn't why he came here and he briefly considered drinking the man to dust. "Get out of here. Go home."

He watched the car speed away and turned back to the tunnel under the over pass. It was boring waiting by himself and maybe he wanted to fight a little with the other whores over stupid things like territory or the proper amount of snugness for a cockring. If this was going to happen, he was only interested in a certain kind of john anyway and who knew when that would show up.

Eying the women carefully, he avoided their glares as he leaned against the wall and sighed.

 _Damnit Stefan._

o0o0o

He turned away seven other cars over the next two hours. His female colleagues shot him a withering glare each time. He heard their whispers about him being ungrateful and giving the spot a bad reputation, but as usual, he was massively disinterested in what people thought of him.

It was around that time a silver Porsche turned the corner towards them. The girls stood straighter, pushed their boobs out and tried to look less used-up. Damon merely crossed his arms. The car stopped and the passenger window rolled all the way down. A woman tottered forward in her ridiculous heels and leaned into the opening briefly before turning away, glaring at Damon.

"He wants you."

Damon smirked, bypassing the woman without coming into contact with her. "Of course he does." Figuring he'd be disappointing another misguided suburbanite Damon took his time. He made his way over to the window, leaning his hands against the edge.

To his surprise, the man behind the wheel wasn't at all what he expected.

"What's a guy like you doing a in a place like this?" He tried for a playful tease, but it lacked his usual bravado.

Mostly in shadow, only Damon could make out the smirk on the man's face. "Get in."

"Tsk. I don't think you can afford me, sweetheart."

"I wasn't asking." The reply was smug, like he was used to getting his way. It demanded Damon's attention, intriguing him. Instantly his plans of turning everyone away changed.

Pretending to think about it, Damon looked around the road. He had been stuck waiting for whatever Stefan had planned long enough. If Stefan insisted he do this, he might as well stop half-assing it and get into character. With a glance back to the driver he ran his tongue over his teeth. Might be worth it.

Shooting the wilted women a smug smile of his own he made the decision.

He opened the passenger door and slid in, eyeing the driver. He was young, but obviously strong. Soft hair with a firm chin and a classic renaissance beauty. There was also a roguish glint in his eyes that made Damon think about being a little worried. Just how he liked them. He supposed he should feel guiltier. If Stefan wanted him to do this, well, who was he to argue? With a blink, he flipped the switch and stopped worrying about his brother.

He turned slightly and ran his hand down the driver's strong thigh, then back up to his groin before the man slapped his hand away. So, it was going to be like that.

Damon leaned up to the man's ear, sliding a hand around his arm. He smelled like expensive cologne and warm blood. "What do I call you?"

The man only laughed. "Does it matter?"

Pulling away, Damon righted himself in the passenger seat. "Just want to know what name to be screaming out in a bit."

The man shot Damon what could only be described as a lecherous grin. "How about, 'Matthew'?"

Damon grimaced. "Nevermind, no names. We'll just have to wait and see whose name I cry out."

Looking back to the road, the man pulled the car into gear and headed off. "Guess so."


	2. The seduction

They arrived at a hotel. Nicer than the by-the-hour joints down town, but not quite upscale enough to give Damon a Pretty Woman complex. The man led Damon without a word out of the parking garage and over to the elevator. Every time Damon reached out to touch him, after all, that was suppose to happen, the man simply brushed him off without saying anything. By the time they reached the floor he was intending to step off on, Damon was considering leaving. If the guy didn't want him, what was the point?

Damon leaned heavily into the wall of the elevator as the doors opened. It was getting boring. The man turned, just once, eyeing Damon and smirking. Still silent, he held the door open and looked pointedly between Damon and the hallway.

It was the smirk that did him in. It was a level of teasing Damon hadn't been aware existed. And it was fucking working. There was something about this 'Matthew.' He wanted to run his fingers through the man's hair, over his body, to taste him. Every time the man brushed him off, Damon was a little bit more interested. Now that he knew it was foreplay, well, that was just fucking awesome.

At the door to a room, the man pulled out a key and took a slow look down both sides of the hallway. Wary, Damon looked as well. The scent of humans permeated the whole building, the reused sheets, and stale laundry of all the guest masked whatever other scents could be lingering. He could hear televisions, and snoring and people talking, but nothing seemed out of the ordinary.

Damon looked back to see the man was inside the room, pulling off his jacket and toeing his shoes off. With an eye roll, Damon walked in. At lease he didn't have to wait to be invited into a hotel room, or he'd be stuck in the hall all night. He kicked the door closed behind him and licked his lips, itching for a drink. Being confused and turned on made him feel unsettled.

As if reading his mind, the man walked over to him with two glasses of scotch and pressed one into Damon's hand. Smiling briefly, he looked Damon in the eye and took a sip from his own glass. Hesitating, Damon sniffed the liquid briefly, always cautious, and took a sip himself. Just really excellent scotch. He could appreciate the man's fine taste.

'Matthew' watched him carefully, then turned and sat on the bed. He knocked back the rest of the alcohol in his glass, did well to hide his wince, then turned and settled himself in the middle of the bed.

"Undress." He commanded while stretching both hands out over the mattress.

It was the first word spoken since Damon got in the car. It was strange, stilted, and still Damon wanted to please this man. He slid the stupid vest off and hung it over the side chair. He stepped closer to the bed, hands going to his fly. He supposed he should be making this more of a striptease, make the man more aroused, but the preliminaries seemed too mundane for this guy.

The man just tilted his head to the side and raked his eyes over Damon's body. The pure Want in his eyes, and the way he was already sprawled out on the bed, with an obvious bulge in his pants like an invitation made Damon's cock twitch. What did it take to be so comfortable with a whore?

He ran his fingers through his hair and looked intently at Damon's hands as they unzipped. "You're pretty gorgeous." His hard stare briefly softened.

Smirking, Damon unceremoniously dropped his pants and stepped out of them. "You're already paying for it. You don't have to seduce me."

His eyes dimmed slightly, "Right." He pulled up, and got off the bed, standing directly in front of Damon. His hands went to Damon's shoulders, feeling each muscle as his hands slid down to Damon's wrists. He brought their hands to his waistband, and Damon instantly got the hint.

Mouth curving slightly, Damon undid the man's pants, his arousal beneath the linen pressing hard against the zipper. "Although it's your money so I guess you can do whatever you want." He slid his hands up the man's shirt, undoing the rest of the buttons. He glanced up to meet bright eyes staring back, studying him. There was something dangerous lurking in there that only excited Damon more. A warm chill licked down his spine and his thoughts strayed to Stefan. This whole thing was his little brother's fault. "Thanks though. Guess it's nice to be appreciated." It was stupid to be hesitant. Ignoring why he was feeling tentative, he focused back down to push the pants off.

They were both hard, the man's cock wet and jutting towards him. Eager, but Damon didn't mind. He placed a wide palm square on the man's chest and pressed him back down into the mattress. The obvious firmness in his muscles and smoothness in his skin was a velvet tease against Damon's fingers. He leaned down, whispering into the man's ear, "You gonna put that body of yours to use already?"

With a serene but confident smile, the younger man curled his hand around Damon's neck and pulled him down between his legs. He tilted his head again and in a blink his smile turned vicious as his face went dark and veiny and fangs descended. "Oh yes." He lurched up against Damon's neck.

"Oh," was all Damon could get out.

 _Fucking vampires._

The teeth broke the tender skin on his shoulder and he winced slightly before his own face went black. "Didn't know it was going to be that kind of night." He wasn't as put off as he thought he should be. The power and strength seemed at least equal to his own, if not slightly weaker. Damon could take him. As the man drank, Damon realized he was actually turned on more. He knew there was a reason that should be wrong, but he just couldn't remember what that reason was. So he cupped his hand around the man's head, keeping them pinned together.

Not to be outdone by the decidedly erotic attack, Damon swiped his tongue over his lips before his own fangs dropped. He turned and bit into the neck exposed to him and took a deep pull as he felt the rush and burn of blood leaving his shoulder. The taste exploded across his tongue and Damon finally reached out and wrapped his hand around the other's cock.

The vampire pulled back, Damon's blood dripping down his chin. "I was hoping it would go like this." With a fierce hunger clouding his face, he grabbed Damon's shoulders and flipped them around, Damon's teeth scraping out of his neck. They tangled together, Damon panicking briefly for control before he decided to just let go, and see what happened. The vampire turned him onto his stomach and straddled his thighs. The heavy cock rested in the crook of his ass.

 _Oh shit._

(tbc)


	3. The payoff

"You're the talent here sweetheart. We're doing this my way."

The gruff words rattled through Damon's head and sent a jolt straight to his groin. Dazed and startled if only for a moment, Damon shook his head and started paying attention. With a determination to enjoy this new experience, he arched back slightly, rolling his hips and testing his limits beneath his companion.

The vampire slid off Damon's legs, farther back so Damon could move but his hands gripped Damon's thighs, sliding up his ass. "Get up." He commanded, sending a chill down Damon's spine.

Damon got up to his knees, knowing to keep them spread. He let his head hang down, seeing a glimpse of knees behind his legs. It was fingers pressing into his hips, thumbs spreading over a tight ring of muscle that was taking all his focus. He had a lot less control than he was used to, but he was strangely okay with it.

It was a thumb, or at least Damon figured it was thumb that entered him first. There wasn't much formality in stretching him open, and apparently the vampire knew there didn't need to be. It wasn't gentle either. It was always the appeal of the unbreakable. The limit had to be pushed as far as possible for anything to be felt at all. Fingertips were digging, digging into his hips as the other thumb split him.

Then something wet swiped across his ass surprising him. Habit made him assume the wet tip of his partner's cock made contact as he readjusted, but no. It was too thoroughly wet and broad.

 _His tongue._

The vampire was roughly stretching him open and had licked the swell of his ass. Damon wasn't sure how to respond to that, except he thought it was maybe… fucking _hot_.

Then it happened again. The vampire traced his tongue over the cleft of Damon's ass, right above the place his thumbs met, into the small of his back, then followed the furrow of Damon's spine. Over and over, reaching higher until lips rested against his shoulder.

"Fuck, you taste good." A puff of breath in the husky words lit up the back of Damon's neck and his hips automatically bucked forward.

He hated doing anything as embarrassing as panting. Stefan was probably the only one in the world who got that reaction naturally out him, but he knew if he said anything now it would be breathy and rough. But his elbows were shaking, holding himself up too long, lust burning through him, his cock achingly heavy. It was worth the risk of sounding a little desperate.

"Enough." He sucked in a stuttered breath. "Just do it. Fuck." He let his elbows give out, falling forward onto his arms, his ass pressing back harder against the vampire's hands, stretching him wider.

There were too many sensations, his body tingling, his cock twitching, he wanted to come right then and the guy had barely started. A memory of these positions reversed slammed into him. It wasn't time for that line of thinking, and again Damon wondered what Stefan had planned when he initiated all this. Then the hands left his ass and he felt a tongue trace the spot the fingers left and he stopped thinking about his brother, because Stefan would never do that. He closed his eyes, pressing his forehead into his arms and gasped to no one in particular. "Fuck, who are you?"

Soft laughter behind him, not menacing, but the laugh of genuine enjoyment warmed Damon. He pulled his spread his legs a little bit farther.

"Does it really matter?"

Damon figured no, it really didn't matter, it's not like he gave his own name at any point. But the thought got choked up as the vampire slammed into him. It burned in the kind of way that doing something bad felt really incredible.

As he slid out, he pulled Damon's back up against his chest, scrambling their legs around so they were both on their knees. It was a sudden kind of manhandling Damon wasn't braced for, and as he was slammed into again, he slumped his head against the shoulder behind him, rolling his hips to counter each thrust. He tried to keep his body loose, clenching only on the exit and relaxing on the entrance. Eyes closed, mouth hanging open, cock leaking as it throbbed in rhythm with each push into him, soaking in the pleasure, he knew he looked utterly debauched.

That was pretty hot too.

He wasn't sure how long it had gone on in the kneeling position, or the various positions they twisted into following it. It was a downside, sort of, the stamina of a vampire. Except it felt so fucking amazing, it was hard to regret anything. Neither of them touched Damon's cock as they continued. Damon planned on putting it to better use than his hand, and figured his partner felt the same way. They didn't speak again, didn't need to until finally the guy wrapped his arms tight around Damon's waist, hips slowing as he released with a muffled groan against Damon's neck.

Damon's hands were knotted in the man's hair, his own neglected cock hardening again at the sound of the sustained moan in his ear. Looking over his shoulder, their eyes focused on each other's and Damon's lips curved into a wicked smile.

"My turn."

It wasn't a question, but the other vampire nodded with a smile of his own. He let his softened dick slide out and they rearranged again, Damon's ass leaking over his leg. He regarded it briefly and looked up at Damon with only a pleased expression. He leaned forward, as if to go for a kiss, but Damon pulled away. He didn't want to be kissing strangers, no matter how sexy they were.

For that split second, Damon could only think about Stefan, which pissed him off. It wasn't fair that his brother/lover/best friend saturated every intimate moment he was having, but he couldn't look at his current partner and not think of him. With a grunt, he pushed the vampire's side, encouraging him by touch alone to turn onto his stomach so Damon wouldn't have to look at his face. Gratefully, unlike his brother, the vampire complied without a word.

It didn't take long to get him ready and Damon easily slid between his legs. Pulling his fingers out, Damon forced himself to ask once. "Lube?"

"Fuck it."

If that was an answer or a command, Damon shrugged and spat into his hand. It was a bit sloppy but the intensity wasn't lost by it. It was a relief, to force his cock into the tight heat. The friction he had been missing was a welcome pressure and the soft sounds of the one beneath him pushing back only urged him along.

Damon moved, thrusting harder because he could. Because his brother had always held his hip, reminding him to slow down and enjoy it, that it wasn't just fucking. This time, with this man, it could be anything Damon wanted it to be because he was supposed to be a whore and the vampire was supposed to be a stranger. And because it was another vampire who wouldn't die from being split in half, Damon went for rough. He knew this was the part Stefan had meant they were missing. They didn't have the cheapness and the filthiness of just fucking because it all meant too much.

Rolling his eyes at himself for letting his thoughts stray again he doubled over, pulling the man's legs obscenely apart. He didn't care, didn't want to care. It was a great that the guy was beautiful spread out beneath him. It was even a bonus he seemed to be fucking enjoying it. Maybe it was a curse of all vampires to not get the depraved sex they needed to feel a little more alive. It couldn't last long anyway. Damon was on a hairpin trigger, itching for release since they first stripped down.

He ran his hands over his partners back, feeling each muscle clench and shake. Hands sliding over familiar hipbones and squeezing. It only took a few more thrusts, and finally Damon came, teeth sinking into the vampire's back at the same time. It wasn't so much a vampire need for blood, as it was Damon's need to claim. He licked once at the wound as his bitten lover cried out in surprise. Damon dropped his head to the broad planes of skin and muscle beneath him to rest a moment as he felt each spurt release.

His lips and fingers were rimmed with blood from where they dug into the vampire, but the wounds were gone moments later when Damon pulled out and fell to the side. It was only things like magical healing that really reminded Damon that he was with a vampire and not just some man. He licked the blood off his fingers, the sweet flavor bursting in his mouth. He gave a pleased hum and looked up to find glassy fucked-out eyes staring back at him.

"Damn that's hot." The man whispered, watching with heavy eyelids as Damon licked each finger clean. "You're a lot more... thorough than I'd expected from someone turning tricks."

Damon huffed a laugh. The irony wasn't lost on him. Pushing up on his side, propping his head up, Damon rested his hand over the guy's hip where he had previously left indentions. The guy didn't flinch and the trust Damon knew was there twisted something inside him. "Yeah well. Something about you is a lot more interesting than the regular john."


	4. The end

The man's lip twitched and Damon realized he liked thinking of him as a man instead of a vampire. The roles were getting all fucked up and Damon wondered why he bothered with them at all. The vampire stared hard back at Damon, stroking his hand lightly up Damon's arm until it came to a rest on his shoulder.

"That was fun. You don't do this often."

It was said matter-of-factly and Damon couldn't argue. He shook his head slowly, wary of revealing too much. His silence seemed to urge on the man.

"Being a whore doesn't suite you. You don't give up control well. Not for anyone."

"Not typically, no." Damon glared back, convincing himself to be angry. It didn't work. The whole discussion was ridiculous and his gaze faltered before changing to a smile. "I'm considering relenting on that."

The man scratched his chin and considered Damon more severely. "You'd be remiss to continue making that decision."

Laughing silently Damon rose off the bed til he was sitting up propped on one hand. "Oh, I have no doubt. But as for now, it's working out pretty well for me."

The look that crossed through the man's expression, that combination of mystified and delighted, made something in Damon's stomach swoop-clench. It was never suppose to come to this, but how could he stop it now? He wanted to lean in closer, let their lips brush together, but Stefan was very insistent on the rules. No kissing was at the top of the list. Kissing was intimate. This was just fucking.

Damon wondered if that was still the case. Their gaze lingered, Damon's hand curling over the man's hip until his fingers brushed over the small of his back.

"What are you doing?"

Damon wanted more. His skin was alive and everything touching it tingled. But he knew the rules. Whores weren't really paid for sex; they were paid to leave. No matter how much he liked the guy. "Guess I better not get too comfortable." He pulled his hand back and made to leave. The hand that that smacked down onto his stomach stopped him.

"Stay."

"Yeah?"

With a peaceful smile the man turned up to face him. All signs of the monster were gone and even the haunted shadows under his eyes were faded. His hand slid down pinning Damon's midsection. "You're not going anywhere tonight, I may want another round."

Damon smiled and his eyes widened a little as bent to look the guy in the eye. "Well well well, I didn't know you had that kind of money or I wouldn't have wasted my time with my other clients tonight." He leaned back down into the bed, making himself comfortable.

With a sigh, the man pulled back getting out of bed to walk into the bathroom.

Listening to the water run, Damon closed his eyes. He blew out a low breath and bent his arms behind his head. Moments later a warm wet rag was running over Damon's body, removing traces of their exchanges. He opened one eye, smiling softly. "I think that's my job?"

With a huff, the man tossed the washcloth over his shoulder, dragging his eyes down Damon's clean bare body. "Right." He leaned over Damon, arm and leg stretching over him until they were face to face. He smirked once; staring down at Damon's mouth then finished his shift to Damon's other side until he fell face first into the empty part of the bed.

"I really should be going."

With a low possessive growl the sleepy man pulled himself up and half spread over Damon's body. "Stay," he murmured again.

Smiling softer, Damon flicked the dark blond hair behind an ear. "You treat all your whores like this? Didn't know you cared, Stefan." He felt the smile in the kiss pressed to his chest and sighed happily.

"Just you, Damon."

Their roles finally cast off, Damon sighed with relief. He untucked one arm and wrapped it around his brother's shoulders, keeping their bodies pinned together. "This was the craziest idea you've ever had." He dragged his tongue across his bottom lip. "And kinky as hell."

Stefan's head bounced off the pillow. A smile that should have been accompanied by a blush crossed Stefan face, and his gaze dropped. "Yeah." Stefan looked up again, locking eyes with Damon. "Was hoping you liked it. We gotta mix it up every half century or so, don't you think?" He looked away again, lowering his head and nuzzling under Damon's chin, he wrapped himself tighter around Damon's body.

Stefan was right. It hadn't been like this between them for a while. Damon laughed, "S'long as it's you and me, apparently I'll do anything you want." He paused for a moment, letting the night wash over him. "Not the last time then? Or only with mysterious stranger person?"

Stefan turned, leg draping over Damon's thighs. "Oh, it'll happen again."

Tightening his arm around Stefan's shoulders, he pressed his lips to his little brother's temple, kissing down to his ear. "So fucking hot."

"I know it wasn't exactly what I promised. I figured you aren't suppose to trust a stranger, or be trusted in return so you might not have given in as easily. But I didn't want you holding back because we don't do these things."

"It felt like you were a different person. That's why you got kinky?"

"No," Stefan rolled his eyes. "I did that because I always wanted to."

"Hmmm my naughty boy."

Wiping his hand down his face, Stefan leveled his gaze again. "Just wanted to give you something different."

Damon wanted to tell Stefan he was perfect, that he never had to change, but if this was what happened when Stefan got creative, well Damon wouldn't stop him. "How am I supposed to say no to that?"

Stefan grabbed Damon's neck, pulling their faces close. "You're not." He closed the distance between them, crushing their lips together. He opened his mouth against Damon's, deepening the kiss. He rolled farther over Damon's body, digging his hands into his brother's hair. They kissed hungrily, letting the final barrier of their game fall away.

Minutes, maybe hours later, neither could be sure, Damon was running his tongue over the hollow of Stefan's neck, arms wrapped tightly around his waist. Stefan laughed, fingers tightening in the nape of Damon's hair. Damon finally pulled back, one brow raised in question.

"You wouldn't kiss me before, not when I was Matthew."

He just smiled, leaning in to briefly brush their lips together again. "Of course I didn't. I couldn't stop thinking about you."

"Funny how that works."

"You were supposed to be someone else. Matt, of all ridiculous people." Damon rolled his eyes and Stefan only smiled.

"I felt stupid that I couldn't do those things with you. This was a good way of trying things out."

"Yeah, me too. It was weird trying to stay in character. Kept thinking I needed to look over my shoulder, waiting for you to barge in all jealous."

Stefan smirked. "Maybe next time you'll lure a real john and we try it your way."

The idea that Damon would be with anyone else, even for a little while, was preposterous and they both knew it. Instead he eyed his brother carefully. "You're my pimp now?"

"Hmm I should be. I'd do well to remember to raise your rates." He stopped and looked back towards the door and his eyes fell on the chair. "Oh man, that vest."

Damon smacked Stefan in the back of the head. "It was your idea!"

Stefan took the hit, laughing louder. "I'm so sorry." He barely managed to get the words out, his hands looping around Damon's waist.

Shaking his head slowly, Damon cupped Stefan's face and pressed their lips together again. "Make it up to me."

Wide-eyed, letting the laughter die out and their closeness rule the moment, Stefan ran his nose along his brother's jaw. "You said my name you know."

Brow furrowing, Damon tilted his head. "When?"

"When you came, you said 'Stefan'."

"Obviously." Smiling softly, Damon slid their lips together.

 _ **The End**_


End file.
